Canadian Pat. No. 895,398 discloses reacting a mole of an unsaturated hydrocarbon group of 700 to 10,000 molecular weight with 1 to 1.5 moles of chloro-substituted maleic or fumaric acid, which material can then be further reacted with alcohol.
U.S. Pat. No. 3,927,041 discloses reacting a mole of 300 to 3,000 molecular weight polybutene containing 5 to 200 ppm 1,3 dibromo-5,5-dialkylhydantoin as a catalyst reacted with 0.8 to 5, generally 1.05 to 1.15 moles of dicarboxylic acid or anhydride, to form materials which can be used per se, or as esters, amides, iraides, amidines, in petroleum products.
U.S. Pat. No. 3,215,707 discloses reacting chlorine with a mixture of polyolefin up to 50,000 molecular weight, especially of 250 to 3,000 molecular weight with one or more moles of maleic anhydride depending upon whether one or more succinic anhydride radicals are to be in each polymer molecule.
U.S. Pat. Nos. 4,113,639 and 4,116,876 disc lose an example of alkenyl succinic anhydride having a molecular weight of the alkenyl group of 1,300 and a Saponification Number of 103 (about 1.3 succinic anhydride units per hydrocarbon molecule). This alkenyl succinic arthydride may be reacted with polyamine and then boric acid ('639), or may be reacted with amino alcohol to form an oxazoline ('876) which is then borsted by reaction with boric acid.
U.S. Pat. No. 4,062,786 in Example 13 shows a polyisobutenyl succinic anhydride of molecular weight of about 1,300 and a Saponification Number of about 100 (about 1.25 succinic anhydride units per alkenyl group).
U.S. Pat. No. 4,123,373 in Example 3 shows a polyisobutenyl succinic anhydride of about 1,400 molecular weight having a Saponification Number of 80 (about 1.07 succinic anhydride units per polyisobutylene units).
Certain metal salts of alkenyl succinic acid are known. For instance, U.S. Pat. No. 3,271,310 teaches that a "metal salt of hydrocarbon-substituted succinic acid having at least 50 aliphatic carbon atoms as the hydrocarbon substituent, the metal of the metal salt being selected from the class consisting of Group I metals, Group II metals, aluminum, lead, tin, cobalt and nickel" is useful as a dual purpose additive.
Similarly, U.S. Pat. No. 4,552,677 discloses a similar material in which the preferred metal in the salt is copper and the hydrocarbon substituent contains from 8 to 35 carbon atoms.
U.S. Pat. No. 4,234,435 discloses that certain of the salts disclosed in U.S. Pat. No. 3,271,310 are useful as dispersant/detergents and viscosity improving agents in lubricating oil compositions. The salts include those in which the polybutene moiety had a H.sub.n of from about 1,300 to about 0 a M.sub.w /M.sub.n ratio of between 1.5 and 4.0 and in which the ratio of the succinic moiety to the polybutene substituent is at least 1.3.
U.S. Pat. No. 3,714,042 relates to the treatment of basic metal sulfonate complexes, sulfonatecarboxylate complexes and carboxylate complexes with high molecular weight carboxylic acids to prepare additives useful in lubricating oils and gasolines. The patentee teaches the ineffectiveness of preformed metal salts of high molecular weight carboxylic acids for such treatments, and exemplifies the sediment formation resulting from use of the calcium salt of polyisobutenyl succinic anhydride at low concentrations in a mineral lubricating oil.